100780-24-3Relevant academic research and scientific papers
Synthesis and Stereochemical Analysis of Planar-Chiral (E)-4-[7]Orthocyclophene
Igawa, Kazunobu,Machida, Kouhei,Noguchi, Kyouhei,Uehara, Kazuhiro,Tomooka, Katsuhiko
, p. 11587 - 11593 (2016)
An efficient synthesis of (E)-4-[7]orthocyclophene (E)-1 via photochemical isomerization of (Z)-1 has been achieved. The key intermediate (Z)-1 was synthesized from commercially available 2-(hydroxymethyl)benzenepropanol (3) in five steps: (i) group-selec
Copper-catalyzed enantioselective intramolecular alkylboron allylic alkylation
Hojoh, Kentaro,Shido, Yoshinori,Ohmiya, Hirohisa,Sawamura, Masaya
supporting information, p. 632 - 635 (2018/04/23)
A reductive CC-bond-forming cyclization of vinyl-terminated allyl chlorides via alkene hydroboration with 9-BBN-H followed by Cu-catalyzed asymmetric intramolecular allylic alkylation with a new chiral phosphoramidite ligand produced six-membered ring com
(Phenylsulfonyl)allenes as substrates for cycloaddition reactions: Intramolecular cyclizations onto unactivated alkenes
Padwa, Albert,Meske, Michael,Murphree, S. Shaun,Watterson, Scott H.,Ni, Zhijie
, p. 7071 - 7080 (2007/10/02)
The reaction of a series of allyl-substituted bis(phenylsulfonyl)methanes or dimethyl malonates with 2,3-bis(phenylsulfonyl)-1,3-butadiene in the presence of base afforded alkenyl-substituted allenes in good yield. The reaction proceeds by initial attack of the soft carbanion onto the terminal position of the diene, and this is followed by PhSO2- elimination to give the phenylsulfonyl-substituted allene. Themal [2 + 2]-cycloaddition proceeded across the C1-C2 double bond of the allene with completely sterospecificity. Stepwise bonding prefers to occur in a 1,6-exo manner rather than in a 1,7-endo fashion. Substitution at the 7-position of the π-bond causes a crossover in the regioselectivity of the [2 + 2]-cycloaddition process. All products can be rationalized by a mechanism which includes an initial carbon-carbon bond formation involving the central allene carbon to give a diradical intermediate. The product distribution is then determined by the substitution pattern of the alkene and the fate of the diradical intermediate.
SYNTHESIS WITH SULFONES XLIV. STEREOSELECTIVE PREPARATION OF EE 1,3-DIENES BY ELIMINATION OF BENZENESULFINIC ACID FROM E HOMOALLYLIC SULFONES.
Penhoat, C. Herve Du,Julia, M.
, p. 4807 - 4816 (2007/10/02)
The preparation of pure E and Z homoallylic 1,1-disulfones followed by the stereoselective reduction of one sulfonyl moiety afforded pure E and Z homoallylic sulfones respectively.Basic elimination with tBuOK in THF gave the corresponding 1,3-dienes in good yield.This reaction, highly stereoselective in the case of E homoallylic sulfones, has been used in the synthesis of (8E,10E) 8,10-dodecadienol, 10 and (9E)9,11-dodecadienol, 15, insect pheromone components.
